An optically active cyclopropanecarboxylate is an important compound as an intermediate for the production of pharmaceuticals and agrochemicals. For example, (+)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid known as chrysanthemum-monocarboxylic acid constitutes an acid component of synthetic pyrethroid type insecticides. (+)-2,2-Dimethylcyclopropanecarboxylic acid is known to be useful as an intermediate for synthesis of β-lactam type antibiotics.
Conventional methods known to produce the optically active cyclopropanecarboxylic acid derivatives directly by synthetic means are a method of reacting a prochiral olefin with a diazoacetate in the presence of an asymmetric copper complex using optically active bis[2-(4,5-diphenyl-1,3-oxazolynyl)]methane as a ligand (Tetrahedron Lett., 32, 7373, 1991 etc.).
These methods, however, were not always satisfactory as an industrial production method in that complicated procedures were required to produce the copper complex and handling thereof was not always easy because of its poor stability.